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WPR I Solutions - APPROVED SOLUTION CADET SECTION/HR TIME...

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APPROVED SOLUTION CADET SECTION/HR TIME OF DEPARTURE _ DEPARTMENT OF CHEMISTRY & LIFE SCIENCE CH383,2007-2008 Chapters: 1-4, 12 WPR I, A Hour Experiment: 1 20 September 2007 INSTRUCTIONS 1. Do not mark on this exam or open it until "begin work" is given. 2. Solve problems in the space provided. SHOW ALL WORK. ANSWER ALL QUESTIONS. 3. Molecular model kits are permitted; however, models may only be assembled after "begin work" is given. The molecular model instruction booklet is not permitted. RDCs and calculators are authorized. 4. There are 9 pages in this exam. Report any illegible or missing pages to the OIC in the hallway. Write your name in the spaces provided. 5. You will have up to 120 minutes to complete the WPR. (TOTAL WEIGHT: 200 POINTS) DO NOT WRITE IN THIS SPACE PROBLEM MAX SCORE CUT YOUR SCORE I 60 II 50 III 40 IV 50 EXTRA CREDIT 20 TOTAL GRADE 200
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Name: ,P,.FPHOVED SOLUTION ------------- Problem I, Fundamentals, 60 (10) 1. Match the term with the definition by placing the correct letter in the blank. A. Orbital F. Stereoisomerism K. Sigma bond B. Unsaturated G. gauche-conformation L. Pi bond C. Aliphatic H. Molecular orbital (MO) theory M. Inductive effect D. anti-conformation 1. Electronegativity N. Constitutional isomer E. Antibonding orbital J. Hybrid orbital O. Saturated a.~ A description of covalent bond formation as resulting from a mathematical combination of atomic orbitals (wave functions) to form molecular orbitals. b. K A covalent bond formed by head-on overlap of atomic orbitals. c. J" An orbital derived from a combination of atomic orbitals. (" 0" d.~ A molecule that has only single bonds and thus can't undergo addition reactions. e. JJ- The geometric arrangement around a carbon-carbon single bond in which the two largest substituents are 180 0 apart as viewed in a Newman projection. (6) 2. Draw the structure of the following. a. 5-ethyl-3,4-dimethyloctane b. 3-cyc1obutylpentane ~1~'Y/"'" /"-'r I ! i 6 (6) 3. Write the name of the following structures. a. b. _-+-( I, I r-'.I, .' (9) 4. Draw the condensed, skeletal, and Kekule (line-bond) structure for 2-methylpentane. Condensed Structure Skeletal Structure Kekule (line-bond) Structure CH383, AY08-1 1 WPRI, A Hour
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------------ ~"f Name: Problem I continued (5) 5. For the molecule CF 4 : a. Draw the Lewis structure, showing all lone pairs of electrons. ·.F:· ~ , J ~. 'r,' L" r:', .0' .4' .. b. The hybridization of the C atom is: c. The F-C-F bond angles should be approximately: --'.-1_, _ d. The geometry around the C atom is: -----'--1_· ' _ (2) 6. Write the ground state elec.~on configuration for sulfur and circle the valence electrons. " r, ( r"' \ \ l) ,-;: I , .-'". '-I '/ ---_ .. ...' (11) 7. For the acetate ion: a. Draw the Kekul~ structure and the resonance structure(s). Use wedges and dashes to show the three-dimensional geometry where necessary. _ . I \ ! I : I) - . , " ~ j\;~ b. Calculate the formal charge of the C connected to the oxygen and both 0 atoms. Show your work. (LL (. )' (11) 8. Consider the following compound which is a pain reliever sold in drug stores as Tylenol.
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